A guest was hurt in my party. I paid his medical bill. Is this expense deductible in the U.S.? If so, where does it go on 1040 Schedule A?
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No, unless the guest is your spouse or dependent. From the IRS:
If you itemize your deductions for a taxable year on Form 1040, Schedule A (PDF), Itemized Deductions, you may be able to deduct expenses you paid that year for medical and dental care for yourself, your spouse, and your dependents.